Holiday Rentals in Windsor

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Windsor holiday rentals

A Pleasant Retreat- No Cleaning Fee & New Discounts

A Pleasant Retreat- No Cleaning Fee & New Discounts
Sun Prairie
10.0 out of 10, Exceptional, (269 reviews)
"Everything about our stay was great. The hosts were very accommodating, had many amenities and suggestions for things to do, along with being around to assist if we had any questions! "
United States
Michaela K.
The price is €271
includes taxes & fees
22 Feb - 23 Feb
A Pleasant Retreat- No Cleaning Fee & New Discounts

Lakeview Cabin > Unique Mid-Century Tucked in Bluff

Lakeview Cabin > Unique Mid-Century Tucked in Bluff
Merrimac
9.8 out of 10, Exceptional, (25 reviews)
"Beautiful property with a perfect view for fall color. Very comfortable and great space for both couples and family. We enjoyed a very relaxing stay. Host was very prompt with responses and easy to work with."
United States
Jenel S.
The price is €319
includes taxes & fees
22 Feb - 23 Feb
Lakeview Cabin > Unique Mid-Century Tucked in Bluff

Enjoy Nature with Full Comfort!

Enjoy Nature with Full Comfort!
Verona
9.2 out of 10, Wonderful, (39 reviews)
"Clean very friendly nice spot"
Canada
Oliver H.
Enjoy Nature with Full Comfort!

King Suite | Free Breakfast. Pool and Hot Tub

King Suite | Free Breakfast. Pool and Hot Tub
Middleton
8.0 out of 10, Very good, (5 reviews)
"Great place for a stay."
United States
Andy D.
The price is €123
includes taxes & fees
1 Mar - 2 Mar
King Suite | Free Breakfast. Pool and Hot Tub

Cannery Square Unit - 106 by Patriot Properties

Cannery Square Unit - 106 by Patriot Properties
Sun Prairie
9.4 out of 10, Exceptional, (28 reviews)
"Great place "
United States
Armando
The price is €280
includes taxes & fees
22 Mar - 23 Mar
Cannery Square Unit - 106 by Patriot Properties

Citys EDGE of Madison- SLEEPS 10 & ONLY 6 Miles to downtown

Citys EDGE of Madison- SLEEPS 10 & ONLY 6 Miles to downtown
Sun Prairie
10.0 out of 10, Exceptional, (13 reviews)
"Beautiful spacious property, extremely clean and excellent host!"
United States
Jen F.
The price is €486
includes taxes & fees
22 Feb - 23 Feb
Citys EDGE of Madison- SLEEPS 10 & ONLY 6 Miles to downtown

2 Bedroom - Main Street Sun Prairie WI

2 Bedroom - Main Street Sun Prairie WI
Sun Prairie
9.6 out of 10, Exceptional, (38 reviews)
"Great location! It worked for what we needed. "
United States
Jeanie B.
2 Bedroom - Main Street Sun Prairie WI

King Suite. Free Breakfast. Pool with a Slide. Close to Olbrich Botanical Gardens!

King Suite. Free Breakfast. Pool with a Slide. Close to Olbrich Botanical Gardens!
Fitchburg
The price is €130
includes taxes & fees
22 Mar - 23 Mar
King Suite. Free Breakfast. Pool with a Slide. Close to Olbrich Botanical Gardens!

Cannery Square Short Term Rentals -102 by Patriot

Cannery Square Short Term Rentals -102 by Patriot
Sun Prairie
8.0 out of 10, Very good, (12 reviews)
"Was cute neighborhood and everything was very clean and close by"
United States
Bri
Cannery Square Short Term Rentals -102 by Patriot

Snowy Madison Escape | Warm Executive Home

Snowy Madison Escape | Warm Executive Home
Fitchburg
10.0 out of 10, Exceptional, (20 reviews)
"Property was generally clean, spacious and had all the amenities that our family needed.An enjoyable stay at a nice property!"
United States
Kim & Jeff T.
The price is €600
includes taxes & fees
22 Feb - 23 Feb
Snowy Madison Escape | Warm Executive Home

Waters Edge Cottage

Waters Edge Cottage
Merrimac
8.2 out of 10, Very good, (11 reviews)
"Won $500 pull tab this weekend. Would stay again."
United States
Ryan R.
Waters Edge Cottage

Charming 3-bedroom Duplex unit with WiFi in Cottage Grove

Charming 3-bedroom Duplex unit with WiFi in Cottage Grove
Village of Cottage Grove
10.0 out of 10, Exceptional, (9 reviews)
"Stayed with friends for the weekend and really enjoyed the home. It was comfortable and had great amenities for our group!"
United States
Anakin F.
The price is €380
includes taxes & fees
22 Feb - 23 Feb
Charming 3-bedroom Duplex unit with WiFi in Cottage Grove

Madison Lakefront Oasis in the Heart of Madison - Central, Minutes to Downtown!

Madison Lakefront Oasis in the Heart of Madison - Central, Minutes to Downtown!
Monona
9.8 out of 10, Exceptional, (47 reviews)
"It was lovely to be by the lake and have the view from the living room along with gas fireplace. So relaxing even in the off season."
United States
Justine K.
The price is €421
includes taxes & fees
22 Feb - 23 Feb
Madison Lakefront Oasis in the Heart of Madison - Central, Minutes to Downtown!

Doty ★ Walk to Everything -Hotel Quality- Downtown

Doty ★ Walk to Everything -Hotel Quality- Downtown
Downtown Madison
9.8 out of 10, Exceptional, (38 reviews)
"We enjoyed having an apartment downtown vs. staying in a hotel. The kids toys and high chair were a nice special touch! Beds are very hard. "
United States
Jenna H.
The price is €249
includes taxes & fees
23 Feb - 24 Feb
Doty ★ Walk to Everything -Hotel Quality- Downtown

Pool with Slide. Great for Business Travelers!

Pool with Slide. Great for Business Travelers!
Fitchburg
The price is €119
includes taxes & fees
22 Mar - 23 Mar
Pool with Slide. Great for Business Travelers!

Free Breakfast Pool & Hot Tub. Near UW-Madison

Free Breakfast Pool & Hot Tub. Near UW-Madison
Madison
10.0 out of 10, Exceptional, (1 review)
"It was comfortable and clean and the staff was so nice. It was well located and the pool and hot tub were lovely as well."
United States
Joy E.
The price is €233
includes taxes & fees
12 Mar - 13 Mar
Free Breakfast Pool & Hot Tub. Near UW-Madison

The Dylin

The Dylin
4.0 star property
Tenney-Lapham
9.4 out of 10, Exceptional, (126 reviews)
"Check in was easy, the room was super clean and cute, great amenities, close to the Sylvee and other bars/restaurants and the lake. Would stay again!! "
United States
Caitlin
The price is €131
includes taxes & fees
22 Mar - 23 Mar
The Dylin

Capital City- 6 Miles from Madison with fireplace

Capital City- 6 Miles from Madison with fireplace
Sun Prairie
9.8 out of 10, Exceptional, (37 reviews)
"Very clean and very spacious house. Great neighborhood and location. "
United States
Sharon M.
The price is €534
includes taxes & fees
22 Feb - 23 Feb
Capital City- 6 Miles from Madison with fireplace

Pet Friendly Fully Furnished Modern 1-Bedroom Oasis with Private Outdoor Retreat

Pet Friendly Fully Furnished Modern 1-Bedroom Oasis with Private Outdoor Retreat
Middleton
10.0 out of 10, Exceptional, (2 reviews)
"We had a fantastic stay at this property, and it truly exceeded our expectations. The location is excellent—perfectly situated with convenient access to both the east and west sides of Madison, making it easy to get wherever we needed to go. The owners were incredibly helpful and responsive, answering the few questions we had quickly and kindly, which made the entire experience even smoother.One of the biggest highlights for us was the private fenced-in area, which was absolutely perfect for our...
United States
Jessi P.
The price is €297
includes taxes & fees
28 Feb - 1 Mar
Pet Friendly Fully Furnished Modern 1-Bedroom Oasis with Private Outdoor Retreat

Entire 3 Bedroom with Fireplace - sleeps 12

Entire 3 Bedroom with Fireplace - sleeps 12
Sun Prairie
9.8 out of 10, Exceptional, (16 reviews)
"The beds were super comfortable and the house had a lot of space. Tami was very helpful and communicative with the check in and check out process."
United States
Noah D.
The price is €507
includes taxes & fees
22 Feb - 23 Feb
Entire 3 Bedroom with Fireplace - sleeps 12
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Save an average of 15% on thousands of hotels when you're signed in

Top Windsor Hotel Reviews

Find out more about Windsor

Everything you need to know about Windsor holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Windsor holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Windsor holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Windsor holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Windsor. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Windsor holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Windsor holiday rentals we have selected for you start as low as €131 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Windsor rentals

At Expedia, we put the best Windsor holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Windsor rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Windsor holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Windsor. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find a holiday rental in Windsor?

Yes, there are holiday rentals in Windsor close to Mousehouse Cheesehaus, or you can select a more secluded option if you're looking for a relaxing stay. Our travellers say Windsor has a good selection of restaurants. Make sure you have time to check out the shopping and sporting events during your trip.

What are some of the best holiday rentals that Windsor has to offer?

4 Bed, 3 Bath w/ Pool, Hot Tub, Gym, Fire Pit on Lake Windsor Golf Course: This highly rated holiday home rental in Windsor offers an outdoor pool, a fireplace and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with 1 hot tub and a selection of books.

What can I see and do in Windsor?

Explore the area and family-friendly sights such as Mousehouse Cheesehaus, or get out into nature at a spot like Olbrich Botanical Gardens. In the wider area, you’ll find East Towne Mall and Madison Area Technical College.

What are holiday rentals like in Windsor?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Windsor. Holiday rentals feature extras such as WiFi and washers and dryers so you'll have all the conveniences of home. If you're concerned about cleanliness, holiday rentals can provide a sense of security away from shared hotel lifts and busy reception areas while still allowing you a great travel experience. You'll also find more space in a holiday rental than in a hotel, which makes a holiday rental a great option for a family getaway.